EP0999239B1 - Hals enthaltende hybridfarbstoffe - Google Patents

Hals enthaltende hybridfarbstoffe Download PDF

Info

Publication number
EP0999239B1
EP0999239B1 EP99811010A EP99811010A EP0999239B1 EP 0999239 B1 EP0999239 B1 EP 0999239B1 EP 99811010 A EP99811010 A EP 99811010A EP 99811010 A EP99811010 A EP 99811010A EP 0999239 B1 EP0999239 B1 EP 0999239B1
Authority
EP
European Patent Office
Prior art keywords
alkyl
hydrogen
aryl
phenyl
compound according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP99811010A
Other languages
English (en)
French (fr)
Other versions
EP0999239A2 (de
EP0999239A3 (de
Inventor
Bansi Lal Kaul
Bruno Piastra
Jean Christoph Graciet
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant Finance BVI Ltd
Original Assignee
Clariant Finance BVI Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Clariant Finance BVI Ltd filed Critical Clariant Finance BVI Ltd
Publication of EP0999239A2 publication Critical patent/EP0999239A2/de
Publication of EP0999239A3 publication Critical patent/EP0999239A3/de
Application granted granted Critical
Publication of EP0999239B1 publication Critical patent/EP0999239B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/08—Naphthalimide dyes; Phthalimide dyes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/14—Benzoxanthene dyes; Benzothioxanthene dyes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S525/934—Powdered coating composition

Definitions

  • the present invention rotates to novel colorants for the mass coloring of polymers.
  • mass coloring of polar polymers examples being polyamides, polyesters, polycarbonates and ABS
  • stringent requirements in terms of their heat stability and light fastness are expected from the dyes used.
  • the object of the present invention is, therefore, to provide heat-stable, light-fast and readily polymer-soluble colorants, with fluorescence property.
  • the invention provides a compound of the formula (I) in which
  • Preferred compounds of the formula (I) are those in which each R 1 and each R 2 is methyl.
  • R 3 is hydrogen, methyl, ethyl, C 1-4 alkylcarbonyl or C 2-4 alkenylcarbonyl, more preferably hydrogen.
  • R 4 as a bridging group is preferably -NHCOphenyl-, -NHSO 2 phenyl- with the phenyl group bonded to the nitrogen atom of the heterocyclic system.
  • R 6 , R 7 , R 8 , R 9 are independently hydrogen, chlorine, bromine, methoxy, ethoxy, phenoxy, -NH-C 6 H 4 -OCH 3 , - O-C 6 H 4 -OCH 3 or -S-C 6 H 4 -OCH 3 .
  • X is preferably sulphur and n is preferably 1 or 2.
  • the present invention also provides a process for preparing the compounds of the formula (I), characterized in that a dicarboxylic acid of the formula (II) or, preferably, one of its functional derivatives, e.g. the acid anhydride or acid halide, is condensed with an amine or the salt of an amine of the formula (III)
  • Suitable salts of the amine of the formula (III) are the chlorohydrate or the sulphate.
  • Condensation can be conducted without solvent in the melt at temperatures, for instance, of between 150°C and 300°C, preferably up to 250°C, or in an inert solvent at temperatures between 25°C and 300°C, preferably between 100°C and 250°C, in the presence or absence of a catalyst, at atmospheric pressure or under pressure.
  • suitable solvents are relatively high-boiling aliphatic or aromatic, substituted or unsubstituted hydrocarbons, examples being xylene (mixture), biphenyl, nitrobenzene, chlorobenzenes, chloronaphthalene, glycol ethers, organic acids and acid amides, especially dimethylformamide, dimethylacetamide or N-methyl-pyrrolidone. If the dicarboxylic acid of the formula (II) is employed in the form of the free acid it is also possible to use water or a relatively high-boiling alcohol, such as ethylene glycol, as solvent.
  • a relatively high-boiling alcohol such as ethylene glycol
  • catalysts examples include inorganic or organic acids, such as hydrochloric or sulphuric acid, benzenesulphonic, toluenesulphonic acid, or acetic acid.
  • organic acids such as hydrochloric or sulphuric acid, benzenesulphonic, toluenesulphonic acid, or acetic acid.
  • the salts of organic acids such as sodium or potassium acetate, are in many cases also suitable as catalysts.
  • the compounds of the invention are eminently suitable for the coloring of melts of synthetic polar polymers such as, for example, ABS, polyester, polycarbonate or polyamides.
  • Polyamides are, for example, polycondensation products or addition polymerization products of dicarboxylic acids and diamines, e.g. of adipic acid and hexamethylenediamine, of lactams, e.g. ⁇ -caprolactam, or of aminocarboxylic acids, e.g. ⁇ -aminoundecanoic acid.
  • the polyamide melt mixed with the pigment is brought into its final form by conventional methods - for example, in melt spinning, injection molding, extrusion or film blowing machines.
  • novel dyes of formula (I) give a fluorescent coloration in synthetic polar polymers such as, for example, ABS, polyester, polycarbonate or polyamides.
  • novel dyes of the formula (I) are extremely stable to the heat stress which is necessarily part of the coloring of synthetic polyamides, and the substrates mass-colored with them also display excellent fastness properties, especially light fastness. Their high polymer-solubility is particularly noteworthy.
  • novel compounds of the formula (I) are also suitable as colorants in electrophotographic toners and developers, such as one- or two-component powder toners (also called one- or two-component developers), magnetic toners, liquid toners, polymerization toners and specialty toners (literature: L.B. Schein, "Electrophotography and Development Physics”; Springer Series in Electrophysics 14, Springer Verlag, 2 nd Edition, 1992).
  • Typical toner binders are addition polymerization, polyaddition and polycondensation resins, such as styrene, styrene-acrylate, styrene-butadiene, acrylate, polyester and phenol-epoxy resins, polysulphones, polyurethanes, individually or in combination, and also polyethylene and polypropylene, which may comprise further constituents, such as charge control agents, waxes or flow assistants, or may be modified subsequently with these additives.
  • polyaddition and polycondensation resins such as styrene, styrene-acrylate, styrene-butadiene, acrylate, polyester and phenol-epoxy resins, polysulphones, polyurethanes, individually or in combination, and also polyethylene and polypropylene, which may comprise further constituents, such as charge control agents, waxes or flow assistants, or may be modified subsequently with these additives.
  • novel compounds of the formula (I) are suitable, furthermore, as colorants in powders and powder coating materials, especially in triboelectrically or electrokinetically sprayable powder coating materials which are used for the surface coating of articles made, for example, from metal, wood, plastic, glass, ceramic, concrete, textile material, paper or rubber (J.F. Hughes, "Electrostatics Powder Coating” Research Studies, John Wiley & Sons, 1984).
  • Powder coating resins that are typically employed are epoxy resins, carboxyl- and hydroxyl-containing polyester resins, polyurethane resins and acrylic resins, together with customary hardeners. Combinations of resins are also used. For example, epoxy resins are frequently employed in combination with carboxyl- and hydroxyl-containing polyester resins.
  • Typical hardener components are, for example, acid anhydrides, imidazoles and also dicyanodiamide and its derivatives, blocked isocyanates, bisacylurethanes, phenolic and melamine resins, triglycidyl isocyanurates, oxazolines and dicarboxylic acids.
  • novel compounds of the formula (I) are suitable as colorants in ink-jet inks, both aqueous and non-aqueous, and in those inks which operate in accordance with the hotmelt process.
  • 16.7 parts of benzo[k,l]thioxanthene-3,4-dicarboxylic anhydride are suspended in 150 parts of N,N-dimethylacetamide. 15.15 parts of the following amine and 0.1 parts of para -toluenesulfonic acid are then added to the suspension, and then heated at reflux for 24 hours. The suspension is then cooled to 25°C and filtered. The cake is washed with dimethylacetamide, alcohol and dried. This gives 22.8 parts of an orange-colored powder.
  • 100 parts of polycaprolactam in the form of a powder are mixed with 0.1 and with 1.0 part respectively of the dye from Example 1 in powder form in a drum mixer. After a short time, the powder is uniformly distributed and adheres to the granules. After about 10 minutes, the mixture is dried at 120°C for 16 hours, transferred to a melt spinning machine and following a residence time of about 8 minutes is spun to fibers at 275-280°C under a nitrogen atmosphere. The yellow-colored fibers are extremely lightfast.
  • Polyester fibers containing 0.5% (w/w) of the colorant described in the example 1 have been prepared and compared against polyester fibers containing 0.5% (w/w) of the S.Y. 98 having the formula according to the following method:
  • the polyester is fused and extruded through a drawing plate at constant rate by gears pump regulation.
  • the spinning machine is heated during 2 hours at temperatures of 260°C, 262°C, 262°C, 265°C and 265°C under pressure of 80 bars.
  • the drawing plate is heated in an oven at 350°C for at least 30 minutes.
  • the obtained fibers are recovered on a bobbin.
  • the fibers colored with our product give a bright fluorescent yellow color with 15% higher color strength compared to S.Y. 98. Light and weather fastness are excellent.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Cosmetics (AREA)
  • Coloring (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (9)

  1. Verbindung der Formel (I)
    Figure 00130001
    worin
    R1
    jeweils -CH3 oder -CH2(C1-4-Alkyl) bedeutet oder zwei Gruppen R1 eine Gruppe -(CH2)5- bilden,
    R2
    jeweils -CH3 oder -CH2(C1-4-Alkyl) bedeutet oder zwei Gruppen R1 eine Gruppe -(CH2)5- bilden,
    R3
    Wasserstoff, C1-8-Alkyl, C3-10-Alkenyl, Phenyl, Phenyl-C1-4alkyl oder -COR5a, wobei R5a Wasserstoff, -C(R10a)=CH2, C1-6-Alkyl, Phenyl, -COOC1-4-Alkyl oder -NR21R22, wobei R10a Wasserstoff oder C1-4-Alkyl, R21 Wasserstoff, C1-12-Alkyl, C5-6-Cycloalkyl, Phenyl, Phenyl-C1-4-alkyl oder C1-12-Alkylphenyl und R22 Wasserstoff oder C1-12- Alkyl,
    R4
    eine direkte Bindung oder ein Brückenglied,
    R5
    Wasserstoff oder C1-4-Alkyl oder
    R4 und R5
    zusammen mit dem sie verbindenden C-Atom ein isocyclisches oder heterocyclisches Brückenelement bilden,
    R6, R7, R8 und R9
    unabhängig voneinander Wasserstoff, Halogen oder R11R12N- oder R12-O- oder R12-S-, wobei R12 C1-C6-Alkyl, C8-C10-Aryl, (C6-C10)-Aryl-(C1-C6)-alkyl oder (C1-C6)-Alkyl-(C6-C10)-aryl, wobei die Alkyl- und/oder Arylreste durch Hydroxy, C1-C6-Alkoxy, C6-C10-Aryloxy oder Halogen substituiert sein können,
    X
    Schwefel, Sauerstoff oder N-R11, wobei R11 Wasserstoff, C1-C6-Alkyl, C6-C10-Aryl, (C6-C10)-Aryl-(C1-C6)-alkyl oder (C1-C6)-Alkyl-(C6-C10)-aryl, wobei die Alkyl- und/oder Arylreste durch Hydroxy, C1-C6-Alkoxy, C6-C10-Aryloxy oder Halogen substituiert sein können,
    n
    eine ganze Zahl von 1 bis 4 inklusive bedeuten.
  2. Verbindung nach Anspruch 1, dadurch gekennzeichnet, dass R1 und R2 Methyl bedeuten.
  3. Verbindung nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass R4 eine direkte Bindung ist.
  4. Verbindung nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass R5 und R3 Wasserstoff bedeuten.
  5. Verbindung nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass R6, R7, R8 und R9 unabhängig voneinander Wasserstoff, Chlor, Brom, Methoxy, Ethoxy, Phenoxy, -NH-C6H4-OCH3, -O-C6H4-OCH3 oder -S-C6H4-OCH3 bedeuten.
  6. Verfahren zur Herstellung einer Verbindung gemäss einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass man eine Dicarbonsäure der Formel (II)
    Figure 00140001
    oder eines ihrer funktionellen Derivate mit einem Amin oder dem Salz eines Amins der Formel (III)
    Figure 00150001
    kondensiert.
  7. Verfahren nach Anspruch 6, dadurch gekennzeichnet, dass man als funktionelles Derivat der Dicarbonsäure das Säureanhydrid oder Säurechlorid einsetzt.
  8. Verwendung einer Verbindung gemäss einem der Ansprüche 1 bis 5 zum Färben von synthetischen Polyamiden, Polyestern, ABS oder Polycarbonaten sowie als Farbmittel in elektrophotographischen Tonern und Entwicklern, in Pulverlacken und in Ink-Jet-Tinten.
  9. Verwendung nach Anspruch 8 zum Massefärben von Polykondensaten aus Dicarbonsäuren und Diaminen, aus Lactamen oder aus Aminocarbonsäuren.
EP99811010A 1998-11-06 1999-11-04 Hals enthaltende hybridfarbstoffe Expired - Lifetime EP0999239B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9824314.0A GB9824314D0 (en) 1998-11-06 1998-11-06 New hetercyclic compounds
GB9824314 1998-11-06

Publications (3)

Publication Number Publication Date
EP0999239A2 EP0999239A2 (de) 2000-05-10
EP0999239A3 EP0999239A3 (de) 2002-03-06
EP0999239B1 true EP0999239B1 (de) 2004-04-07

Family

ID=10841932

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99811010A Expired - Lifetime EP0999239B1 (de) 1998-11-06 1999-11-04 Hals enthaltende hybridfarbstoffe

Country Status (8)

Country Link
US (1) US6277536B1 (de)
EP (1) EP0999239B1 (de)
JP (1) JP2000154190A (de)
KR (1) KR20000035220A (de)
AT (1) ATE263810T1 (de)
DE (1) DE69916213T2 (de)
ES (1) ES2217721T3 (de)
GB (1) GB9824314D0 (de)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9914173D0 (en) 1999-06-18 1999-08-18 Clariant Int Ltd New heterocyclic compounds
GB0103011D0 (en) * 2001-02-07 2001-03-21 Clariant Int Ltd Improvements in or relating to chemical compounds
DE10238994A1 (de) * 2002-08-20 2004-02-26 Basf Ag Rylenfarbstoffe
DE10331178A1 (de) * 2003-07-10 2005-02-17 Dystar Textilfarben Gmbh & Co. Deutschland Kg Tinten für digitalen Textildruck mit reaktiven gelben Fluoreszenzfarbstoffen
JP4734921B2 (ja) * 2004-11-30 2011-07-27 Ｔｄｋ株式会社 有機ｅｌ素子用化合物及び有機ｅｌ素子
JP4734922B2 (ja) * 2004-11-30 2011-07-27 Ｔｄｋ株式会社 アザ−ベンゾアントラセン化合物及びその製造方法
US8236198B2 (en) * 2008-10-06 2012-08-07 Xerox Corporation Fluorescent nanoscale particles
AU2011257238B2 (en) 2010-05-25 2015-01-29 Sicpa Holding Sa Polymer-bonded perylene dyes and compositions containing same
CN101948631B (zh) * 2010-07-17 2016-01-20 青岛大学 一种k型活性耐光橙色偶氮染料及其制备方法
AR086509A1 (es) 2011-05-25 2013-12-18 Sicpa Holding Sa Tintes de quaterrileno y/o terrileno unidos a polimeros y composiciones que los contienen
GEP201706662B (en) 2011-11-10 2017-05-10 Sicpa Holding Sa Polymer-bonded polycyclic aromatic hydrocarbons having nitrogen containing substituents
WO2013075980A1 (en) * 2011-11-23 2013-05-30 Sicpa Holding Sa Polycyclic aromatic compounds containing an s atom or s(=0)2 group and their use as dyes
JP5880410B2 (ja) * 2012-11-29 2016-03-09 富士ゼロックス株式会社 静電荷像現像用透明トナー、静電荷像現像剤、トナーカートリッジ、現像剤カートリッジ、プロセスカートリッジ、画像形成装置及び画像形成方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3888863A (en) * 1970-04-14 1975-06-10 Hoechst Ag Benzoxanthene and benzothioxanthene dyestuffs and process for their manufacture
DE2017764C3 (de) * 1970-04-14 1974-04-04 Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt Benzoxanthen- und Benzothioxanthenfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung. Anmi Farbwerke Hoechst AG, vormals Meister Lucius & Brüning, 6000 Frankfurt
DE2017765C3 (de) * 1970-04-14 1979-08-16 Hoechst Ag, 6000 Frankfurt Tagesleuchtpigmente, deren Verwendung und Verfahren zu deren Herstellung
DE2122975A1 (de) * 1971-05-10 1972-11-30 Farbwerke Hoechst AG, vormals Meister Lucius & Brüning, 6000 Frankfurt Basische Farbstoffe, ihre Herstellung und Verwendung
DE2804530C2 (de) * 1978-02-03 1986-04-30 Hoechst Ag, 6230 Frankfurt Verwendung von wasserlöslichen Benzoxanthenfarbstoffen für fluoreszierende Tinten
JPS59147054A (ja) * 1983-02-09 1984-08-23 Sumitomo Chem Co Ltd テトラメチルピペリジン残基を含有する水不溶性染料
EP0241419B1 (de) * 1986-04-10 1993-05-19 Sandoz Ag Piperidylgruppen enthaltende Pigmente
US4902787A (en) * 1988-04-21 1990-02-20 North Carolina State University Method for producing lightfast disperse dyestuffs containing a build-in photostabilizer [molecule] compound
CH684194A5 (de) * 1991-01-26 1994-07-29 Sandoz Ag Pigmente in Form von intermolekularen Salzen von zwitterionischen Farbstoffen.
JP3447744B2 (ja) * 1994-11-28 2003-09-16 ミネソタ マイニング アンド マニュファクチャリング カンパニー 持続性のある着色及び／又は蛍光特性を示す製品
US6110566A (en) * 1997-10-23 2000-08-29 3M Innovative Properties Company Stabilization of fluorescent dyes in vinyl articles using hindered amine light stabilizers

Also Published As

Publication number Publication date
EP0999239A2 (de) 2000-05-10
JP2000154190A (ja) 2000-06-06
DE69916213T2 (de) 2004-08-05
ATE263810T1 (de) 2004-04-15
EP0999239A3 (de) 2002-03-06
US6277536B1 (en) 2001-08-21
KR20000035220A (ko) 2000-06-26
DE69916213D1 (de) 2004-05-13
ES2217721T3 (es) 2004-11-01
GB9824314D0 (en) 1998-12-30

Similar Documents

Publication Publication Date Title
EP0999239B1 (de) Hals enthaltende hybridfarbstoffe
US6162261A (en) Triphendioxazine
US6046335A (en) Heterocyclic compounds
EP1172418A2 (de) Farbstoffe mit einer Hydroxy-, Carbonsäure-, Carbonsäureester- oder Aminoendgruppe
US6482817B1 (en) Hybrid pigments
US6559306B2 (en) Dye compounds
US6255482B1 (en) Triphendioxazine compounds
EP1447430A1 (de) Neue Monoanthrachinonazamethinfarbstoffe
US6540820B1 (en) Heterocyclic compounds
JP4468356B2 (ja) ベンゾジピロールをベースとする複素環染料
EP1447429A1 (de) Bisanthraquinonazomethinfarbstoffe
EP1422267A1 (de) Farbstoffe auf Basis von Naphthalin-1,4,5,8-Tetracarbonsäuredianhydrid
KR100416015B1 (ko) 아미노퀴나졸린디온계수불용성아조착색제
JP5004591B2 (ja) ２，４−ジオキソピリミジン系メソイオン顔料
EP0559345B1 (de) Polyzyklische Farbstoffe
KR20010087335A (ko) 안료의 제조 방법
GB2114588A (en) Disperse oxazolone dyestuffs

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

AX Request for extension of the european patent

Free format text: AL;LT;LV;MK;RO;SI

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

AX Request for extension of the european patent

Free format text: AL;LT;LV;MK;RO;SI

17P Request for examination filed

Effective date: 20020906

AKX Designation fees paid

Free format text: AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

17Q First examination report despatched

Effective date: 20021230

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

RTI1 Title (correction)

Free format text: HALS CONTAINING HYBRID DYESTUFFS

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20040407

Ref country code: CY

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20040407

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: CH

Ref legal event code: NV

Representative=s name: CLARIANT INTERNATIONAL LTD.

Ref country code: CH

Ref legal event code: EP

REF Corresponds to:

Ref document number: 69916213

Country of ref document: DE

Date of ref document: 20040513

Kind code of ref document: P

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20040707

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20040707

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20040707

ET Fr: translation filed
REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2217721

Country of ref document: ES

Kind code of ref document: T3

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20041104

Ref country code: IE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20041104

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20041104

Ref country code: AT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20041104

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20041105

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MC

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20041130

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20041130

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20041130

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20041130

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed

Effective date: 20050110

BERE Be: lapsed

Owner name: *CLARIANT FINANCE (BVI) LTD

Effective date: 20041130

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20050601

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20050601

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20041104

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20050729

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 20050601

REG Reference to a national code

Ref country code: IE

Ref legal event code: MM4A

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20051104

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20041105

BERE Be: lapsed

Owner name: *CLARIANT FINANCE (BVI) LTD

Effective date: 20041130

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: PT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20040907